US5543083A - Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation - Google Patents

Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation Download PDF

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US5543083A
US5543083A US08/280,685 US28068594A US5543083A US 5543083 A US5543083 A US 5543083A US 28068594 A US28068594 A US 28068594A US 5543083 A US5543083 A US 5543083A
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antioxidant compound
alkyl group
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methyl
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US08/280,685
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Mark R. Sivik
John C. Severns
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Procter and Gamble Co
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Procter and Gamble Co
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Assigned to PROCTER & GAMBLE COMPANY, THE reassignment PROCTER & GAMBLE COMPANY, THE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SEVERNS, JOHN CORT, SIVIK, MARK ROBERT
Priority to DK95925625T priority patent/DK0773922T3/en
Priority to PCT/US1995/008711 priority patent/WO1996003369A1/en
Priority to JP8505771A priority patent/JPH10503491A/en
Priority to CA002363543A priority patent/CA2363543C/en
Priority to DE69522972T priority patent/DE69522972T2/en
Priority to EP95925625A priority patent/EP0773922B1/en
Priority to PT95925625T priority patent/PT773922E/en
Priority to CA002192803A priority patent/CA2192803A1/en
Priority to ES95925625T priority patent/ES2149367T3/en
Priority to DE69517690T priority patent/DE69517690T2/en
Priority to ES99870028T priority patent/ES2161090T3/en
Priority to EP99870028A priority patent/EP0926132B1/en
Priority to CN95194353A priority patent/CN1071310C/en
Priority to AU29694/95A priority patent/AU2969495A/en
Priority to AT95925625T priority patent/ATE194137T1/en
Publication of US5543083A publication Critical patent/US5543083A/en
Application granted granted Critical
Priority to CN99121550.8A priority patent/CN1273265A/en
Priority to GR20000402057T priority patent/GR3034371T3/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/08—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to an acyclic carbon atom of an acyclic unsaturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/14—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to a carbon atom of a six-membered aromatic ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)
  • Fats And Perfumes (AREA)

Abstract

The present invention relates to non-surface staining, light stable antioxidant compounds which reduce the fading, decoloration and degradation of various surfaces, ie., fabrics, from sunlight. These antioxidant compounds are butylated hydroxytoluene and sorbic acid derivatives, containing at least one C8 -C22 hydrocarbon fatty amine organic moiety and are either solid materials having a melting point of less than about 80° Celsius, or are liquids at a temperature of less than about 40° Celsius.

Description

TECHNICAL FIELD
The present invention relates to novel, non-surface staining, light stable antioxidant compounds to reduce the fading, discoloration and degradation of various surfaces, i.e. fabrics, from sunlight. These antioxidant compounds are butylated hydroxytoluene and sorbic acid derivatives, preferably containing at least one C8 -C22 hydrocarbon fatty amine organic moiety and are either solid materials having a melting point of less than about 80° C., or are liquids at a temperature of less than about 40° C. Preferably these antioxidant compounds are incorporated into fabric softening compositions.
BACKGROUND OF THE INVENTION
Consumers worldwide experience color damage to their clothing, upholstery, the interior of their automobiles, etc., from exposure to the sun. For example, color damage to clothing during drying and during wear is especially severe for those consumers living in tropical and subtropical climates. Despite extensive efforts by the industry to develop light stable surfaces such as upholstery, and automobile interiors, to develop light stable dyes, after-treatments to improve light-fastness of dyes for textiles, and plastics which resist fading, the fading of surfaces from sunlight still remains a problem.
Antioxidant compounds are known in the art for various benefits. For example, EPA 273,011, Ravichandran et al., published Jun. 29, 1988, Ciba-Geigy, teaches N,N-bis(hydroxyethyl)hydroxylamine esters to stabilize organic materials (i.e. organic polyolefins, elastomers and lubricating oils) against oxidative, thermal and actinic degradation.
U.S. Pat. No. 5,081,280, Takee et al., issued on Jan. 14, 1992, Yoshitomi Pharmaceutical Industries, Ltd., teaches a process for producing esterified, sterically hindered phenolic compounds as an antioxidant for organic materials with decreased reaction times and less discoloration of the compound. These compounds do not contain an amine function as do the compounds of the present invention.
U.S. Pat. No. 3,330,859, Dexter et al., issued Jul. 11, 1967, Geigy Chemical Corporation, teaches sterically hindered phenolic carboxylic acid esters which are useful to stabilize organic materials such as organic polymers and copolymers, lubricating oils of the aliphatic ester type, hydrocarbon material such as gasoline, etc. These compounds do not contain an amine function as do the compounds of the present invention.
U.S. Pat. No. 3,920,729, Sagawa, et al., issued Nov. 18, 1975, Sumitomo Chemical Co., Ltd., teaches sterically hindered phenolic esterified isopropanolamines for the stabilization of organic substances, particularly polyolefins, halogenated vinyl polymers, copolymers of halogenated vinyl and unsaturated polymerizable compound, copolymers of acrylonitrile, butadiene and styrene, polyurethane, polyamides, polyesters, polyacetals, polycarbonates, polystyrene and natural and synthetic rubber. These compounds have methyl groups attached to the beta carbon atom with regard to the nitrogen atom, for enhanced thermal stability with reduced blooming when mixed with a polyolefin.
U.S. Pat. No. 4,305,868, Wheeler et al., issued December 15, 1981, Uniroyla, Inc., teaches sterically hindered phenolic substituted esterbisamides as antioxidants useful for the protection of organic materials such as synthetic and natural rubbers, plastics and petroleum products against oxidative degradation.
Furthermore, U.S. Pat. No. 4,900,469, Clorox, teaches antioxidants in detergents for bleach stability. Antioxidants have been used in softeners and detergents to prevent fabric yellowing and to control malodor. (See, JP 72/116,783, Kao.)
Because antioxidant compounds are expensive, it is desirable to select and utilize the most efficient compounds in order to minimize the cost of formulating with these compounds.
However, it is now recognized that antioxidants adaptable for various other applications are not always satisfactory for other applications such as for use in foods (as a preservative), cosmetics (as a preservative), in rinse added fabric softener compositions, dryer added fabric softener compositions, detergents, fabric pretreatment or spray on products, hard surface cleaners, compositions for use on floor coverings (i.e. carpet, vinyl), automotive upholstery, upholstery, hair care products, vinyl treatments and plastics.
With regard to textiles, it has now been discovered that visible light is responsible for a significant amount of dye fading on clothing. For example, visible light has a higher contribution to fading than UV-A, which has a higher contribution to fading than UV-B. Antioxidants can provide broader sun-fade fabric protection for surfaces than sunscreen agents because antioxidant effectiveness is not dependent upon the absorption of light.
Therefore, an object of the present invention is to provide antioxidant compounds, effective at low levels, which will reduce the rate of degradation and/or discoloration (i.e. sun-fading) of a variety of surfaces.
All of the above patents and patent applications are incorporated herein by reference.
SUMMARY OF THE INVENTION
The present invention relates to novel antioxidant compounds to reduce the physical or chemical degradation or discoloration of surfaces, especially the fading of a variety of surfaces from sunlight, wherein the antioxidant compound is a non-surface staining, light stable compound, preferably containing at least one C8 -C22 hydrocarbon fatty organic moiety, preferably at least one C12-C 18 hydrocarbon fatty organic moiety; wherein the antioxidant compound is a solid material having a melting point of less than about 80° C., preferably less than about 50° C., or a liquid at a temperature of less than about 40° C.; preferably from about 0° C. to about 25° C.
These antioxidant compounds are derivatives of butylated hydroxytoluene or sorbic acid and are selected from the group consisting of: ##STR1## wherein each R1 and R3 is selected from the group consisting of hydroxy, methoxy, ethoxy, propoxy, butoxy, methyl, ethyl, propyl, straight or branched chained butyl groups, straight or branched chained amyl groups, and mixtures thereof, preferably straight or branched chained butyl groups, straight or branched chained amyl groups, and mixtures thereof, and more preferably "tert"-butyl groups;
R2 is a hydroxy group;
each R4 and R7 is selected from the group consisting of a saturated or unsaturated C1 -C22 -alkyl, aryl, cyclic alkyl group, (which may be interrupted by an ester, amide, or ether group), hydrogen, and mixtures thereof, preferably a methyl group;
each R5, R6, R8, and R9 is selected from the group consisting of a saturated or unsaturated C1 -C22, alkyl, aryl, cyclic alkyl group (which may be interrupted by an ester, amide, or ether group), preferably a C8 to C22 alkyl group more preferably a C12 to C18 alkyl group, and even more preferably a C12 to C14 alkyl group, and mixtures thereof;
n is from 1 to 50, preferably from 1 to 10, more preferably 1;
Y is a hydrogen or a methyl group; and
Z is a hydrogen or a methyl group.
The amino group of the compounds of Formulas I to IV can be protonated or quaternized with R10 X wherein R10 is a hydrogen, a C1 to C6 alkyl group, a C1 to C6 hydroxy alkyl group, preferably a C1 to C3 alkyl group or hydroxy alkyl group, e.g. methyl (most preferred), ethyl, propyl, hydroxyethyl, and the like, benzyl group, and mixtures thereof; and X- is the anion of a strong acid, for example chloride, bromide, methylsulfate, formate, sulfate, nitrate, and the like.
All percentages and ratios used herein are by weight of the total composition.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to novel antioxidant compounds to reduce the physical or chemical degradation or discoloration of surfaces, especially the fading of a variety of surfaces from sunlight, wherein the antioxidant compound is a non-surface staining, light stable compound, preferably containing at least one C8 -C22 hydrocarbon fatty organic moiety, preferably at least one C12 -C18 hydrocarbon fatty organic moiety; wherein the antioxidant compound is a solid material having a melting point of less than about 80° C., preferably less than about 50° C., or a liquid at a temperature of less than about 40° C.; preferably from about 0° C. to about 25° C.
These antioxidant compounds are derivatives of butylated hydroxytoluene or sorbic acid and are selected from the group consisting of: ##STR2## wherein each R1 and R3 is selected from the group consisting of hydroxy, methoxy, ethoxy, propoxy, butoxy, methyl, ethyl, propyl, straight or branched chained butyl groups, straight or branched chained amyl groups, and mixtures thereof, preferably straight or branched chained butyl groups, straight or branched chained amyl groups, and mixtures thereof, and more preferably "tert"-butyl groups;
R2 is a hydroxy group;
each R4 and R7 is selected from the group consisting of a saturated or unsaturated C1 -C22, alkyl, aryl, cyclic alkyl group, (which may be interrupted by an ester, amide, or ether group), hydrogen, and mixtures thereof, preferably a methyl group;
each R5, R6, R8, and R9 is selected from the group consisting of a saturated or unsaturated C1 -C22, alkyl, aryl, cyclic alkyl group (which may be interrupted by an ester, amide, or ether group), preferably a C8 to C22 alkyl group, more preferably a C12 to C18 alkyl group, and even more preferably a C12 to C14 alkyl group, and mixtures thereof;
n is from 1 to 50, preferably from 1 to 10, more preferably 1;
Y is a hydrogen or a methyl group; and
Z is a hydrogen or a methyl group.
The amino group can be protonated or quaternized with R10 X wherein R10 is a hydrogen, a C1 to C6 alkyl group, a C1 to C6 hydroxy alkyl group, preferably a C1 to C3 alkyl group or hydroxy alkyl group, e.g. methyl (most preferred), ethyl, propyl, hydroxyethyl, and the like, benzyl group, and mixtures thereof; and X- is the anion of a strong acid, for example chloride, bromide, methylsulfate, formate, sulfate, nitrate, and the like.
Preferably each R1 and R3 is a straight or branched chain butyl group and mixtures thereof; R4 is a methyl group; R5 is selected from the group consisting of a saturated or unsaturated C12 to C18 alkyl group; and n is 1.
More preferably, each R1 and R3 is a "tert"-butyl group; R5 is selected from the group consisting of a saturated or unsaturated C12 to C14 alkyl group; and n is 1.
An especially preferred compound of the present invention is 2-(N-methyl-N-cocoamino)ethyl 3', 5'-di-tert-butyl-4-hydroxybenzoate.
The antioxidant compounds of the present invention demonstrate light stability. "Light stable" means that the antioxidant compounds of the present invention do not discolor when exposed to either sunlight or simulated sunlight for approximately 2 to 60 hours at a temperature of from about 25° C. to about 45° C.
Antioxidant compounds and free radical scavengers can generally stabilize surfaces and/or protect dyes from degradation or discoloration by first preventing the generation of singlet oxygen and peroxy radicals, and thereafter terminating the degradation pathways. Not to be limited by theory, a general discussion of the mode of action for antioxidants and free radical scavengers is disclosed in Kirk Othmer, The Encyclopedia of Chemical Technology, Volume 3, pages 128-148, Third Edition (1978), which is incorporated herein by reference in its entirety.
Methods of Manufacture
The following examples further describe and demonstrate embodiments within the scope of the present invention. The examples are given solely for the purpose of illustration and are not to be construed as limitations of the present invention, as many variations thereof are possible without departing from the spirit and scope of the invention.
EXAMPLE 1
N-methyl-N-(2-hydroxyethyl)cocoamine in the amount of 15.64 g (63.3 mmol) is dissolved in 200 mL of dichloromethane and the resulting solution heated to 40° C. Following addition of triethylamine in the amount of 6.41 g (63.3 mmol), 3,5-di-tert-butyl-4-hydroxybenzoyl chloride in the amount of 17.00 g (63.3 mmol) is added to the solution so as to maintain the reaction temperature at 35°-40° C. The reaction mixture is stirred for an additional 2 h at 40° C. and then cooled to room temperature. After stirring 16 h, the solution containing the reaction product is filtered and the filtrate concentrated. The resulting residue is re-dissolved in 300 mL of chloroform and washed twice with two 50 mL aliquots of 50% K2 CO3 in water. The organic layer is separated, dried over MgSO4, filtered, and concentrated. The product is purified by column chromatography. Purity of the product is determined by thin layer chromatography and the structure confirmed by 13 C NMR.
EXAMPLE 2
N,N-bis-(2-hydroxyethyl)-cocoamine in the amount of 22.09 g (78.1 mmol) and triethylamine in the amount of 15.79 g (156.3 mmol) are dissolved in 100 mL of dichloromethane. The resulting solution is treated with 3,5-di-tert-butyl-4-hydroxybenzoyl chloride in the amount of 42.00 g (156.3 mmol) dissolved in 100 mL of dichloromethane. During addition the reaction temperature is maintained between 35°-400° C. The reaction mixture is stirred for an additional 60 min at reflux and then cooled to room temperature. The mixture is filtered and the filtrate concentrated. The resulting residue is redissolved in 200 mL of dichloromethane and washed twice with two 100 mL aliquots of 50% K2 CO3 in water, once with 100 mL of saturated NaHCO3 solution in water, and once with 100 mL of brine. The organic layer is separated, dried over MgSO4, filtered, and concentrated to give a viscous oil. Purity of the product is determined by thin layer chromatography and the structure confirmed by 13 C NMR.
EXAMPLE 3
N-methyl-N-(2-hydroxyethyl)cocoamine in the amount of 36.28 g (144.0 mmol) and triethylamine in the amount of 14.62 g (144.0 mmol) are dissolved in 250 mL of dichloromethane. The resulting solution is treated with 2,4-trans-trans-hexandienoyl chloride in the amount of 18.80 g (144.0 mmol). During addition, the reaction temperature is maintained between 35°-40° C. The reaction mixture is stirred for an additional 2 h at reflux and then cooled to room temperature. The mixture is filtered and the filtrate concentrated. The resulting residue is re-dissolved in 300 mL of dichloromethane and washed twice with 200 mL of 50% K2 CO3 in water and twice with 200 mL of saturated NaHCO3 solution in water. The organic layer is separated, dried over MgSO4, treated with activated charcoal, filtered, and concentrated to give an oil. Purity of the product is determined by thin layer chromatography and the structure confirmed by 13 C NMR.
COMPOSITIONS
The present invention also relates to a composition for decreasing the physical or chemical degradation of surfaces, comprising:
(A) an effective amount of an antioxidant compound; and
(B) an effective amount of a carrier material; wherein the antioxidant compound is selected from the group consisting of: ##STR3## wherein each R1 and R3 is selected from the group consisting of hydroxy, methoxy, ethoxy, propoxy, butoxy, methyl, ethyl, propyl, straight or branched chained butyl groups, straight or branched chained amyl groups, and mixtures thereof, preferably straight or branched chained butyl groups, straight or branched chained amyl groups, and mixtures thereof, and more preferably "tert"-butyl groups;
R2 is a hydroxy group;
each R4 and R7 is selected from the group consisting of a saturated or unsaturated C1 -C22, alkyl, aryl, cyclic alkyl group (which may be interrupted by an ester, amide, or ether group), hydrogen, and mixtures thereof, preferably a methyl group;
each R5, R6, R8, and R9 is selected from the group consisting of a saturated or unsaturated C1 -C22, alkyl, aryl, cyclic alkyl group (which may be interrupted by an ester, amide, or ether group), preferably a C8 to C22 alkyl group, more preferably a C12 to C18 alkyl group, and even more preferably a C12 to C14 alkyl group, and mixtures thereof;
n is from 1 to 50, preferably from 1 to 10, more preferably 1;
Y is a hydrogen or a methyl group; and
Z is a hydrogen or a methyl group.
The amino group can be protonated or quaternized with R10 X wherein R10 is a hydrogen, a C1 to C6 alkyl group, a C1 to C6 hydroxy alkyl group, preferably a C1 to C3 alkyl group or hydroxy alkyl group, e.g. methyl (most preferred), ethyl, propyl, hydroxyethyl, and the like, benzyl group, and mixtures thereof; and X- is the anion of a strong acid, for example chloride, bromide, methylsulfate, formate, sulfate, nitrate, and the like.
The carrier and/or diluent employed in the instant compositions is a non-toxic, non-irritating substance which when mixed with the antioxidant compound, promotes the deposition of the antioxidant compound onto surfaces. The compositions of the present invention preferably comprise from about 25% to about 95%, preferably from about 50% to about 90% of a liquid carrier. Preferably the carrier and/or diluent is primarily water due to its low cost relative availability, safety, and environmental compatibility. The level of water in the liquid carrier is at least about 50%, preferably at least about 60%, by weight of the carrier. Mixtures of water and low molecular weight, e.g., <100 g/mol, organic solvent, e.g., lower alcohol such as ethanol, propanol, isopropanol or butanol are useful as the carrier liquid. Low molecular weight alcohols include monohydric, dihydric (glycol, etc.) trihydric (glycerol, etc.), and higher polyhydric (polyols) alcohols.

Claims (11)

What is claimed is:
1. An antioxidant compound, to reduce the degradation or discolorntion of surfaces from sunlight, selected from the group consisting of: ##STR4## and mixtures thereof wherein each R1 is selected from the group consisting of hydroxy, methoxy, ethoxy, propoxy, butoxy, methyl, ethyl, propyl, straight or branched chained butyl groups, and straight or branched chained amyl groups;
each R2 is a hydroxy group;
each R3 is selected from the group consisting of hydroxy, methoxy, ethoxy, propoxy, butoxy, methyl, ethyl, propyl, straight or branched chained butyl groups, and straight or branched chained amyl groups;
each R4 is selected from the group consisting of a saturated or unsaturated C1 -C22 alkyl, aryl, or cyclic alkyl group, and hydrogen;
each R5 is n saturated or unsaturated C1 -C22 alkyl, aryl, or cyclic alkyl group;
each R6 is a saturated or unsaturated C1 -C22, alkyl, aryl, or cyclic alkyl group;
n is from 1 to 50;
Y is a hydrogen or a methyl group; and
wherein the amino group of the compounds of Formulas I to II, optionally, quaternized with R10 X when R10 is a hydrogen, a C1 -C6 alkyl group, a C1 -C6 hydroxyl alkyl group, benzyl group; and X is an anion from a strong acid.
2. The antioxidant compound of claim 1 wherein the antioxidant compound is a solid material having a melting point of less than about 80° C. or a liquid at a temperature of less than about 40° C.
3. The antioxidant compound of claim 1 wherein the antioxidant compound is a solid material having a melting point of less than about 50° C. or a liquid at a temperature of about 0° C. to about 25° C.
4. The antioxidant compound of claim 3 wherein the compound is 2-(N-methyl-N-cocoamino)ethyl 3',5'-di-tert-butyl-4-hydroxybenzoate.
5. The antioxidant compound of claim 1 wherein each R1 and R 3 is a straight or branched chain butyl group, straight or branched chained amyl group, and mixtures thereof; R4 is a methyl group; each R5 and R6 is a saturated or unsaturated C12 to C14 alkyl group.
6. The antioxidant compound of claim 5 wherein each R1 and R3 is a "tert"-butyl group; each R5 and R6 is a saturated or unsaturated C12 to C14 alkyl group.
7. The antioxidant compound of claim 6 wherein the antioxidant compound is selected from the group consisting of Formula I, Formula II and mixtures thereof wherein each R1 and R3 is a "tert"-butyl group; each R5 and R6 is a saturated or unsaturated C12 to C14 alkyl group.
8. The antioxidant compound of claim 7 wherein the antioxidant compound is 2-(N-methyl-N-cocoamino)ethyl 3,5-di-tert-butyl-4-hydroxybenzoate.
9. A composition for decreasing the physical or chemical degradation of surfaces, comprising:
(A) an effective amount for decreasing the physical or chemical degradation of surfaces, of the antioxidant compound of claim 1; and
(B) from about 25% to about 95%, by weight of the composition, of a carrier material.
10. A composition for decreasing the physical or chemical degradation of surfaces, composing:
(A) an effective amount for decreasing the physical or chemical degradation of surfaces, of the antioxidant compound of claim 8; and
(B) from about 25% to about 95%, by weight of the composition, of a carrier material.
11. A composition for decreasing the physical or chemical degradation of surfaces, comprising:
(A) an effective amount for decreasing the physical or chemical degradation of surfaces, of the antioxidant compound of claim 1; and
(B) from about 25% to about 95%, by weight of the composition, of a carrier material.
US08/280,685 1994-07-26 1994-07-26 Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation Expired - Fee Related US5543083A (en)

Priority Applications (18)

Application Number Priority Date Filing Date Title
US08/280,685 US5543083A (en) 1994-07-26 1994-07-26 Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation
DE69517690T DE69517690T2 (en) 1994-07-26 1995-07-13 FATTAMINE DERIVATIVES OF BUTYLATED HYDROXYTOLUEN FOR PROTECTING SURFACES FROM PHYSICAL AND CHEMICAL DEGRADING
EP99870028A EP0926132B1 (en) 1994-07-26 1995-07-13 Fatty amine derivatives of sorbic acid for the protection of surfaces from physical and chemical degradation
JP8505771A JPH10503491A (en) 1994-07-26 1995-07-13 Fatty amine derivatives of butylated hydroxytoluene for protection of surfaces from physical and chemical degradation
CA002363543A CA2363543C (en) 1994-07-26 1995-07-13 Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation
DE69522972T DE69522972T2 (en) 1994-07-26 1995-07-13 Fatty amine derivatives of sorbic acid for the protection of surfaces against physical and chemical degradation
EP95925625A EP0773922B1 (en) 1994-07-26 1995-07-13 Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation
PT95925625T PT773922E (en) 1994-07-26 1995-07-13 FATTY AMIN DERIVATIVES OF BUTYLATED HYDROXYTOLUENE FOR THE PROTECTION OF SURFACES OF PHYSICAL AND CHEMICAL DEGRADATION
CA002192803A CA2192803A1 (en) 1994-07-26 1995-07-13 Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation
ES95925625T ES2149367T3 (en) 1994-07-26 1995-07-13 BUTYLATED HYDROXYTOLUENE FAT AMINE DERIVATIVES FOR THE PROTECTION OF SURFACES AGAINST PHYSICAL AND CHEMICAL DEGRADATION.
DK95925625T DK0773922T3 (en) 1994-07-26 1995-07-13 Fatamine derivatives of butylated hydroxytoluene to protect surfaces from physical and chemical degradation
ES99870028T ES2161090T3 (en) 1994-07-26 1995-07-13 DERIVATIVES OF AMINAS FATS OF SORBIC ACID FOR THE PROTECTION OF SURFACES OF PHYSICAL AND CHEMICAL DEGRADATION.
PCT/US1995/008711 WO1996003369A1 (en) 1994-07-26 1995-07-13 Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation
CN95194353A CN1071310C (en) 1994-07-26 1995-07-13 Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation
AU29694/95A AU2969495A (en) 1994-07-26 1995-07-13 Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation
AT95925625T ATE194137T1 (en) 1994-07-26 1995-07-13 FAT AMIN DERIVATIVES OF BUTYLATED HYDROXYTOLUENE FOR THE PROTECTION OF SURFACES FROM PHYSICAL AND CHEMICAL DEGRADATION
CN99121550.8A CN1273265A (en) 1994-07-26 1999-10-12 Antioxygen compound for reducing surface degradation or decoder and composite containing it
GR20000402057T GR3034371T3 (en) 1994-07-26 2000-09-08 Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation

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US08/280,685 US5543083A (en) 1994-07-26 1994-07-26 Fatty amine derivatives of butylated hydroxy toluene for the protection of surfaces from physical and chemical degradation

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EP (2) EP0926132B1 (en)
JP (1) JPH10503491A (en)
CN (2) CN1071310C (en)
AT (1) ATE194137T1 (en)
AU (1) AU2969495A (en)
CA (1) CA2192803A1 (en)
DE (2) DE69522972T2 (en)
DK (1) DK0773922T3 (en)
ES (2) ES2161090T3 (en)
GR (1) GR3034371T3 (en)
PT (1) PT773922E (en)
WO (1) WO1996003369A1 (en)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5723435A (en) * 1994-07-26 1998-03-03 The Procter & Gamble Company Rinse added fabric softener compositions containing antioxidants for sun-fade protection fabrics
US5733855A (en) * 1994-07-26 1998-03-31 The Procter & Gamble Company Dryer-added fabric treatment article of manufacture containing antioxidant and sunscreen compounds for sun fade protection of fabrics
US6207740B1 (en) 1999-07-27 2001-03-27 Milliken & Company Polymeric methine ultraviolet absorbers
US20030078328A1 (en) * 2001-08-21 2003-04-24 Mason Mary E. Low-color resorcinol-based ultraviolet absorbers and methods of making thereof
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US6602447B2 (en) 2001-08-21 2003-08-05 Milliken & Company Low-color ultraviolet absorbers for high UV wavelength protection applications
US6607994B2 (en) 1999-07-19 2003-08-19 Nano-Tex, Llc Nanoparticle-based permanent treatments for textiles
US20030155559A1 (en) * 2001-08-21 2003-08-21 Connor Daniel M. Thermoplastic containers exhibiting excellent protection to various ultraviolet susceptible compounds
US20040157517A1 (en) * 2002-05-07 2004-08-12 Danielson Todd D. Novel combinations for use as toners in polyesters
US20040214934A1 (en) * 2003-04-28 2004-10-28 Jusong Xia Low-color ultraviolet absorbers for thermoplastic and thermoset high UV wavelength protection applications
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US5723435A (en) * 1994-07-26 1998-03-03 The Procter & Gamble Company Rinse added fabric softener compositions containing antioxidants for sun-fade protection fabrics
US5733855A (en) * 1994-07-26 1998-03-31 The Procter & Gamble Company Dryer-added fabric treatment article of manufacture containing antioxidant and sunscreen compounds for sun fade protection of fabrics
US5763387A (en) * 1994-07-26 1998-06-09 The Procter & Gamble Company Rinse added fabric softener compositions containing antioxidants for sun-fade protection for fabrics
US5869443A (en) * 1994-07-26 1999-02-09 The Procter & Gamble Company Dryer-added fabric treatment article of manufacture containing antioxidant and sunscreen compounds for sun fade protection of fabrics
US5962402A (en) * 1994-07-26 1999-10-05 The Procter & Gamble Company Dryer-added fabric treatment article of manufacture containing antioxidant and sunscreen compounds for sun fade protection of fabrics
US6607994B2 (en) 1999-07-19 2003-08-19 Nano-Tex, Llc Nanoparticle-based permanent treatments for textiles
US6207740B1 (en) 1999-07-27 2001-03-27 Milliken & Company Polymeric methine ultraviolet absorbers
US20030151027A1 (en) * 2001-08-21 2003-08-14 Zhao Xiaodong E. Low-color ultraviolet absorber compounds and compositions thereof
US7097789B2 (en) 2001-08-21 2006-08-29 Milliken & Company Thermoplastic containers exhibiting excellent protection to various ultraviolet susceptible compounds
US6602447B2 (en) 2001-08-21 2003-08-05 Milliken & Company Low-color ultraviolet absorbers for high UV wavelength protection applications
US6559216B1 (en) 2001-08-21 2003-05-06 Milliken & Company Low-color ultraviolet absorber compounds and compositions thereof
US20030078328A1 (en) * 2001-08-21 2003-04-24 Mason Mary E. Low-color resorcinol-based ultraviolet absorbers and methods of making thereof
US20030155559A1 (en) * 2001-08-21 2003-08-21 Connor Daniel M. Thermoplastic containers exhibiting excellent protection to various ultraviolet susceptible compounds
US6596795B2 (en) 2001-08-21 2003-07-22 Milliken & Company Low-color vanillin-based ultraviolet absorbers and methods of making thereof
US6891058B2 (en) 2001-08-21 2005-05-10 Milliken & Company Low-color ultraviolet absorber compounds and compositions thereof
CN100340589C (en) * 2001-08-21 2007-10-03 美利肯公司 Thermoplastic containers exhibiting excellent protection to various ultraviolet susceptible compounds
US20040157517A1 (en) * 2002-05-07 2004-08-12 Danielson Todd D. Novel combinations for use as toners in polyesters
US6875811B2 (en) 2002-05-07 2005-04-05 Milliken & Company Single compound toners for use in polyesters
US20040214934A1 (en) * 2003-04-28 2004-10-28 Jusong Xia Low-color ultraviolet absorbers for thermoplastic and thermoset high UV wavelength protection applications
US7094918B2 (en) 2003-04-28 2006-08-22 Milliken & Company Low-color ultraviolet absorbers for thermoplastic and thermoset high UV wavelength protection applications
US8933131B2 (en) 2010-01-12 2015-01-13 The Procter & Gamble Company Intermediates and surfactants useful in household cleaning and personal care compositions, and methods of making the same
US9193937B2 (en) 2011-02-17 2015-11-24 The Procter & Gamble Company Mixtures of C10-C13 alkylphenyl sulfonates

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GR3034371T3 (en) 2000-12-29
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JPH10503491A (en) 1998-03-31

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